Cationic bleach activator with enhanced hydrolytic stability

Abstract

A novel cationic bleach activator having an enhanced hydrolytic stability is provided. The novel cationic bleach activator also leads to a reduction in strength loss of cotton fibers compared to conventional hot peroxide bleaching, and achieves this reduction in strength loss without a loss of whiteness. Bleaching compositions and detergent compositions comprising the novel cationic bleach activator also are provided. A method of bleaching cellulosic fibers, such as cotton fibers, and a method for removing a stain or discoloration from an article are further provided.

1. A cationic bleach activator of Formula (I): 
       
         
           
           
               
               
           
         
       
       wherein:
 n is an integer from 0 to 3; 
 Q +  is a quaternary nitrogen group; 
 Ar is an aryl group or a substituted aryl group; 
 X is selected from the group consisting of O, S, and NR 1 ; wherein R 1  is selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, and substituted aryl; 
 each R 2  is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, halo, hydroxyl, alkoxyl, aryl, arylkyl, aryloxyl, substituted aryl, and aralkyloxyl; and 
 Z −  is a charge-balancing counter anion and can be present or absent. 
 
     
     
       2. The cationic bleach activator of  claim 1 , wherein Q is: 
       
         
           
           
               
               
           
         
         wherein each R 3  is independently selected from the group consisting of H, alkyl, substituted alkyl, branched alkyl, cycloalkyl, alkylene, hydroxyalkyl, alkoxyalkyl, aryl, substituted aryl, aralkylene, and aralkyl, or 
         two or more R 3  groups together represent a alkyl, aralkyl, alkylene, or aralkyene group; provided that at least one R 3  group is an alkylene or aralkylene group that is covalently attached to the Ar moiety of the compound of Formula (I). 
       
     
     
       3. The cationic bleach activator of  claim 2 , wherein X is O, three R 3  groups are alkyl and one R 3  group is alkylene, and the cationic bleach activator has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       4. A bleaching composition comprising:
 (a) from about 0.1% to about 70% by weight of the composition of a source of hydrogen peroxide; and 
 (b) an effective amount of a cationic bleach activator of Formula (I): 
 
       
         
           
           
               
               
           
         
       
       wherein:
 n is an integer from 0 to 3; 
 Q +  is a quaternary nitrogen group; 
 Ar is an aryl group or a substituted aryl group; 
 X is selected from the group consisting of O, S, and NR 1 ; wherein R 1  is selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, and substituted aryl; 
 each R 2  is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, halo, hydroxyl, alkoxyl, aryl, arylkyl, aryloxyl, substituted aryl, and aralkyloxyl; and 
 Z −  is a charge-balancing counter anion and can be present or absent. 
 
     
     
       5. The bleaching composition of  claim 4 , wherein the cationic bleach activator of Formula (I) has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       6. The bleaching composition of  claim 4 , comprising:
 (a) from about 0.1% to about 50% by weight of the composition of the source of hydrogen peroxide; and 
 (b) from about 0.1% to about 50% by weight of the cationic bleach activator of the formula (I). 
 
     
     
       7. The bleaching composition of  claim 4 , comprising an additive selected from the group consisting of a conventional bleach activator, a transition metal containing bleach catalyst, an optical brightener, a bleach-stable thickener, a detergent builder, a detersive enzyme, a detersive surfactant, a nonionic surfactant, a low-foaming automatic dishwashing surfactant, a laundry detergent surfactant, an anionic surfactant, and combinations thereof, provided that the cationic bleach activator does not react with the anionic surfactant to form a visible precipitate at ambient temperature. 
     
     
       8. The bleaching composition of  claim 7 , wherein the conventional bleach activator is selected from the group consisting of an alkanoyloxybenzenesulfonate, tetraacetylethylenediamine, and combinations thereof. 
     
     
       9. The bleaching composition of  claim 7 , wherein the nonionic surfactant comprises an ethoxylated nonionic surfactant. 
     
     
       10. The bleaching composition of  claim 7 , comprising:
 (a) from about 0.1% to about 10% of the cationic bleach activator of Formula (I); 
 (b) from about 0.5% to about 25% of the source of hydrogen peroxide, wherein the hydrogen peroxide source is in the form of a perborate salt or a percarbonate salt; and 
 (c) from about 0.1% to about 7% of the low-foaming automatic dishwashing surfactant; and 
 wherein the bleaching composition is in a granular automatic dishwashing detergent form. 
 
     
     
       11. The bleaching composition of  claim 7 , wherein the laundry detergent surfactant is selected from the group consisting of a sugar-derived surfactant, a sarcosinate, an amine oxide, and combinations thereof. 
     
     
       12. The bleaching composition of  claim 7 , comprising:
 (a) from about 0.1% to about 10% of the cationic bleach activator; 
 (b) from about 0.5% to about 25% of the hydrogen peroxide source, wherein the hydrogen peroxide source is in the form of a perborate salt or a percarbonate salt; and 
 (c) from about 0.5% to about 25% of the laundry detergent surfactant; and 
 wherein the bleaching composition is in a granular laundry detergent form. 
 
     
     
       13. The bleaching composition of  claim 7 , wherein the detergent builder is selected from the group consisting of a citrate, a layered silicate, zeolite A, zeolite P, and combinations thereof. 
     
     
       14. A detergent composition comprising an effective amount of a cationic bleach activator of Formula (I): 
       
         
           
           
               
               
           
         
         wherein:
 n is an integer from 0 to 3; 
 Q +  is a quaternary nitrogen group; 
 Ar is an aryl group or a substituted aryl group; 
 X is selected from the group consisting of O, S, and NR 1 ; wherein R 1  is selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, and substituted aryl; 
 each R 2  is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, halo, hydroxyl, alkoxyl, aryl, arylkyl, aryloxyl, substituted aryl, and aralkyloxyl; and 
 Z −  is a charge-balancing counter anion and can be present or absent. 
 
       
     
     
       15. The detergent composition of  claim 14 , wherein the cationic bleach activator of Formula (I) has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       16. The detergent composition of  claim 14 , comprising an additive selected from the group consisting of a conventional bleach activator, a detergent builder, a detersive enzyme, a detersive surfactant, a nonionic surfactant, a low-foaming automatic dishwashing surfactant, a laundry detergent surfactant, an anionic surfactant, a fragrance, and combinations thereof, provided that the cationic bleach activator does not react with the anionic surfactant to form a visible precipitate at ambient temperature. 
     
     
       17. The detergent composition of  claim 16 , wherein the conventional bleach activator is selected from the group consisting of tetraacetylethylenediamine, nonanoyloxybenzenesulfonate, and combinations thereof. 
     
     
       18. The detergent composition of  claim 14 , wherein the detergent composition is a laundry detergent composition. 
     
     
       19. The detergent composition of  claim 14 , wherein the detergent composition is a hard surface cleaning detergent composition. 
     
     
       20. A method for bleaching a cellulosic fiber, the method comprising:
 (a) providing one of an aqueous solution, a dispersion, and a slurry comprising a bleaching composition comprising:
 (i) from about 0.1% to about 70% by weight of the composition of a source of hydrogen peroxide; and 
 (ii) an effective amount of a cationic bleach activator of the formula (I): 
 
 
       
         
           
           
               
               
           
         
         wherein:
 n is an integer from 0 to 3; 
 Q +  is a quaternary nitrogen group; 
 Ar is an aryl group or a substituted aryl group; 
 X is selected from the group consisting of O, S, and NR 1 ; wherein R 1  is selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, and substituted aryl; 
 each R 2  is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, halo, hydroxyl, alkoxyl, aryl, arylkyl, aryloxyl, substituted aryl, and aralkyloxyl; and 
 Z −  is a charge-balancing counter anion and can be present or absent; and 
 
         (b) contacting a cellulosic fiber with the one of an aqueous solution, a dispersion, and a slurry comprising the bleaching solution for a period of time. 
       
     
     
       21. The method of  claim 20 , wherein the cationic bleach activator of Formula (I) has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       22. The method of  claim 20 , wherein the cellulosic fiber is selected from the group consisting of a cotton fiber and paper. 
     
     
       23. A method for removing a stain or discoloration from an article, the method comprising:
 (a) providing one of an aqueous solution, a dispersion, and a slurry comprising a bleaching composition comprising:
 (i) from about 0.1% to about 70% by weight of the composition of a source of hydrogen peroxide; and 
 (ii) an effective amount of a cationic bleach activator of the formula (I): 
 
 
       
         
           
           
               
               
           
         
         wherein:
 n is an integer from 0 to 3; 
 Q +  is a quaternary nitrogen group; 
 Ar is an aryl group or a substituted aryl group; 
 X is selected from the group consisting of O, S, and NR 1 ; wherein R 1  is selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, and substituted aryl; 
 each R 2  is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, halo, hydroxyl, alkoxyl, aryl, arylkyl, aryloxyl, substituted aryl, and aralkyloxyl; and 
 Z −  is a charge-balancing counter anion and can be present or absent; and 
 
         (b) contacting an article having the stain or discoloration with the one of an aqueous solution, a dispersion, and a slurry comprising the bleaching solution for a period of time. 
       
     
     
       24. The method of  claim 23 , wherein the cationic bleach activator of Formula (I) has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       25. The method of  claim 23 , wherein the article having the stain or discoloration is selected from the group consisting of a fabric, dishware, a hard surface, and combinations thereof. 
     
     
       26. A method for oxidizing a dye in a residual dyehouse effluent, the method comprising:
 (a) providing one of an aqueous solution, a dispersion, and a slurry comprising a bleaching composition comprising:
 (i) from about 0.1% to about 70% by weight of the composition of a source of hydrogen peroxide; and 
 (ii) an effective amount of a cationic bleach activator of the formula (I): 
 
 
       
         
           
           
               
               
           
         
         wherein:
 n is an integer from 0 to 3; 
 Q +  is a quaternary nitrogen group; 
 Ar is an aryl group or a substituted aryl group; 
 X is selected from the group consisting of O, S, and NR 1 ; wherein R 1  is selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, and substituted aryl; 
 each R 2  is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, halo, hydroxyl, alkoxyl, aryl, arylkyl, aryloxyl, substituted aryl, and aralkyloxyl; and 
 Z −  is a charge-balancing counter anion and can be present or absent; and 
 
         (b) contacting a residual dyehouse effluent with the one of an aqueous solution, a dispersion, and a slurry comprising the bleaching solution for a period of time to oxidize the dye in the residual dyehouse effluent. 
       
     
     
       27. The method of  claim 26 , wherein the cationic bleach activator of Formula (I) has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       28. A method for bleaching a chemically sensitive material, the method comprising:
 (a) providing one of an aqueous solution, a dispersion, and a slurry comprising a bleaching composition comprising:
 (i) from about 0.1% to about 70% by weight of the composition of a source of hydrogen peroxide; and 
 (ii) an effective amount of a cationic bleach activator of the formula (I): 
 
 
       
         
           
           
               
               
           
         
         wherein:
 n is an integer from 0 to 3; 
 Q +  is a quaternary nitrogen group; 
 Ar is an aryl group or a substituted aryl group; 
 X is selected from the group consisting of O, S, and NR 1 ; wherein R 1  is selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, aryl, and substituted aryl; 
 each R 2  is independently selected from the group consisting of H, alkyl, substituted alkyl, cycloalkyl, halo, hydroxyl, alkoxyl, aryl, arylkyl, aryloxyl, substituted aryl, and aralkyloxyl; and 
 Z −  is a charge-balancing counter anion and can be present or absent; and 
 
         (b) contacting a chemically sensitive material with the one of an aqueous solution, a dispersion, and a slurry comprising the bleaching solution for a period of time. 
       
     
     
       29. The method of  claim 28 , wherein the cationic bleach activator of Formula (I) has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       30. The method of  claim 20 , wherein the chemically sensitive material is selected from the group consisting of wool, a man-made cellulosic fiber, and a fiber blend.